If you want to stay at an interesting, Continental-boutique type hotel located near Boystown, check out The Willows on Surf and Broadway. Great value and service. Wherever you stay, don't forget Priceline, which has always served me well, and don't be afraid to bid early, often and low - just like voting in Chicago! Give Chicago Pizza & Oven Grinder Co., located several blocks south on Clark a try, and see if it doesn't change your mind about Chicago-style deep dish pizza. Try any of the Polish buffets near Midway airport if that appeals to you, or some of the several German Bierstuben on Irving Park Rd. A few hours spent browsing Chicago on Yelp will be worth it. Definitely go to the Field, Science & Industry, and Historical Society Museums, and the Art Institute, Adler Planetarium and the adjoining Acquarium. Try to catch a performance of the world-class Chicago Symp. Orchestra; they sound just as magnificent at Friday matinees as they do at other times, and seats are more affordable and available. Try to do w/o a car in the city, though; parking is extortionate and the El and taxis can get you where you need to be quickly and cheaply; not so much for the buses, except for the free shuttles along Michigan Avenue, which is always worth a stroll. You'll have a great time in the town I grew up near, and maybe you'll even luck out and hit a spell of warm weather, which is known to happen during that time of year. Have a great time!